


All I Do Is Win

by Jayenator565



Category: Supergirl (TV 2015)
Genre: F/F, Family Game Night, Fluff, did I mention Lena is a bit of a useless gay?, gay shit, mainly fluff, ok like lowkey it could be crack
Language: English
Status: Completed
Published: 2020-05-03
Updated: 2020-05-03
Packaged: 2021-03-01 18:48:48
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,441
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23981851
Author URL: https://archiveofourown.org/users/Jayenator565/pseuds/Jayenator565
Summary: When it comes to the language of love Jess liked to believe that she was ahead, she was married after all, even had a son. Yet somehow, in some way the disaster lesbian that is her boss Lena Luthor seems to stay winning.Except maybe when it involves a certain blonde-haired reporter.Supercorp from a bit of an outside perspective.
Relationships: (minor) Alex Danvers/Maggie Sawyer, Kara Danvers/Lena Luthor
Comments: 22
Kudos: 282





	All I Do Is Win

**Author's Note:**

  * For [yesiamsleepy](https://archiveofourown.org/users/yesiamsleepy/gifts).



Jess: 16

Lena: 0

"Will that be all Ms. Luthor?"

Jess cleared her throat when she noticed her boss was hardly giving her the time of day, very much enraptured by her phone, and for reasons that weren't related to work.

She would bet anything the soft smile and yearning glance her boss was throwing at her phone was meant for none other than her newest friend. One of her only friends really. 

The only time Jess had seen Lena smile like that lately was when a certain blonde-haired reporter would stop by with potstickers and takeout for lunch.

Ms. Luthor was already so smitten if the smile wasn’t enough to clue Jess in, then the fact that her boss would completely rearrange staff meetings and hours of work in the lab researching just to speak to her new ‘friend’ did it. 

It started off innocent enough. Kara would stop by for a talk about this or that. Maybe a new exciting feature on L Corp’s improvements under Lena’s leadership. Perhaps to invite Lena to a new restaurant that had opened in town. Now that she thought about it, that girl was always eating. She could probably gobble down as much food as a whale.

A very incredibly attractive whale, Jess wasn’t blind. The reporter was a whole snack and she wasn’t afraid to admit it. Maybe a bit afraid to admit it in front of her boss. The Luthors did have a temper and she did not want to be face to face with a jealous Lena Luthor. 

“Ms. Luthor,” The woman finally managed to pull herself away from the tiny piece of technology, but not without one last yearning gaze. 

“Yes, Jess?” The way the older woman struggled to keep her eyes away from the temptation of the phone sitting right beside her hand, Jes would almost think her presence was a burden. Well if Ms. Luthor thought she was going to act like that and not get teased she had another thing coming.

“Sorry, ma’am just wanted to know if you wanted anything else before I let you get back to your girlfriend.” The extra emphasis on that final word and Jess’ not at all subtle eyebrow wiggling was not lost on Lena. Jess would be astounded at how red her boss’ face was turning if she wasn’t already trying to hold in her giggles.

“ _Jess_ i-ca!”

“I’ll take that as a catch you in the morning Ms. Luthor, and oh do you need me to call u-haul?”

“Whatever reason would I have for a u-haul?” Hmm very true, Lena could easily hire a whole team of movers if she and Kara ever got that serious. Of course, first, she’d have to actually admit she was interested in Kara. If only her money could buy her enough vaginal fortitude to finally ask the reporter out on a date. Then Jess wouldn’t have to put up with any more of Lena’s afternoons spent gazing longingly out of her office balcony doors as rain dramatically poured over the city. 

“Don’t worry about it, but before I go please do give Kara my best and just one question?” Jess put on her most innocent face but she knew her boss wasn’t buying it by the suspicious scowl she was wearing.

Plus she could have sworn she heard Lena murmur out, “I can’t really stop you now can I,” just under her breath before nodding her consent.

“Do you think you’ll change your name to Danvers or will she change hers to Luthor for the wedding?”

She really shouldn’t have but the look of Lena Luthor gaping like a codfish was more than worth her hurried run as she found herself dodging flying pens until she made her escape through the door.

Lena Luthor, absolutely speechless. She’d have to bribe old Meg the security guard to send her that footage later.

Jess: 17

Lena: 0

\--

“Have you tried turning it off and on again?”

Lena took a measured breath, gripping the edge of her desk with tensed muscles. Today had been one thing after another, the old men on the Board spent hours berating her, nevermind they wouldn’t even have a Board to be on without her, the prototypes in the labs had failed in spectacular fashion meaning the team would need to start from scratch and now her when all she wanted to do was relax and read some new research her computer had decided it wanted to freeze and blue screen every few minutes. Needless to say, while she accepted Jess as a dear friend any other time, right now the sass was grating on the tiniest bit of the last nerve she had left.

“Jess, I’m a genius, one of the youngest most successful CEO’s in the country, I am a businesswoman, a philanthropist, an entrepreneur-”

A useless lesbian incapable of asking out one woman on a date, Jess coughed, hoping to mask the laugh that wanted to come out after that little thought.

“-of course I-”

“It’s working! I did it!”

Supergirl crawled out from under Lena’s desk looking entirely too pleased with herself. She had stopped by after delivering some robbers to jail when Lena’s depressed sighs caught her ear, “I unplugged everything and put it all back in and look it’s working fine so far... if it goes off again maybe I could call Winn?”

So she turned it off and on again.

Jess: 25

Lena: 0

Jess watched, eyes glimmering with amusement as Lena rushed to reassure Kara that she was sure she had fixed the problem with a dazzling smile. 

She watched as Kara returned the smile with a nervous glance down, adjusting where her glasses would usually be if she was in her civilian clothes, never mind her glasses were always perfectly placed on her face anyway.

She kept watching as Kara made a joke here and Lena laughed there, circling around each other with an unmistakable pull. Like they had their own gravitational force between them. 

She watched as they forgot she even in the room sharing soft touches to wrists and squeezes to shoulders until she decided that ok yea maybe her watching was getting a tad creepy and quietly excused herself.

How were they both so smart and yet so useless?

In any event, she was never lacking for entertainment. And the bets between herself and Jeffrey, Lena’s personal driver, were getting more ludicrous the longer the women took.

As much as she teased and prodded and gave Lena hell, she was glad. Ecstatic really for her friend who was once so closed off that her only company at night was a glass of wine and a documentary. Ms. Luthor had always been kind to her, more than generous, genuinely interested in her family life. It was great to see her finally experience at least some of the happiness she got to feel every day with her own wife. 

And that was the real reason why she joked and nudged because she could tell they really would be great together. The reporter was probably the only person even kinder than Lena. Someone truly selfless. She never asked Lena for anything, if anything all she did was give. She understood how important simply being there was for a person who grew up in a household like the Luthors. Kara cared in a way few people would when faced with Lena’s money or family name. 

That was why Jess would ship them to her dying breath. 

Oh well, maybe tomorrow Lena would finally get her nerve up. Or at least some time within the next month. Preferably before Christmas, or else she was really going to owe Jeffrey and Meg some money.

\--

Lena looked up from where she was so comfortably snuggled into the side of one Kara Danvers. They had binged watched the first few episodes of Killing Eve and after shivering from the temperature drop outside as evening turned to night, Kara had suggested they share the throw blanket on the back of the couch. 

The next thing she knew they were starting season 2 and here she was practically draped over the reporter’s arm.

She could feel Kara’s breath just grazing the side of her neck as she turned to her, “I can pause if that’s an important work thing?”

Lena fought the blush growing at realizing just how close their faces were with their current position sprawled on the couch in her apartment. As much as she loathed it, that was the special tone she had set for Jess’s phone number and if the girl was texting her this late it must be important surely.

She bit her lip clearly warring with herself, she hated to ruin the relaxing mood with the potential stress the text could bring.

Kara, ever observant, easily sent Lena a soft smile and grabbed their discarded cups off the coffee table, “How about I stretch a bit, get a bathroom break and refill our drinks and then you can see what it is that Jess needs. Ok?”

Before she could even open her mouth to respond Kara had pressed a kiss to her forehead practically rendering the CEO speechless and left with a flourish. What did she do to deserve someone as understanding as Kara Danvers in her life? She might never know.

Biting back her ever-growing grin Lena retrieved the damn phone from her purse that lay discarded on the floor. A quick fingerprint and facial scan and she was in the encrypted section of her texts.

Greatest Assistant in the World™: Do you know what one useless lesbian said to the girl she was hopelessly crushing on Ms. Luthor?

…

Lena could hardly explain the sudden urge to just pelt her wretched phone out the window or something. Rolling her eye skyward with a withering sigh she figured she better reply so that Jess could get it out of her system.

Best Boss Ever: I’m sure you will no doubt enlighten me, Jessica

She watched as the dots to indicate typing immediately appeared, no doubt Jess was eagerly awaiting the moment for her newest punchline. 

Greatest Assistant in the World™: Absolutely nothing, that’s why she’s useless.

“Ah,” Lena actually scoffed, of course, she had said many things to Kara, in fact, they have had a plethora of conversations.

“All good in there?” Kara asked, peeking her head from around the corner where the kitchen was.

“Oh just dandy, I’m responding to Jess right now, I’ll show her,” She was so focused on her phone she missed the endearing smile Kara was wearing at her antics. The blonde chuckled softly to herself, returning to her mission of finding Lena’s stash of soda. She knew there was some more of her favorite flavor around here somewhere.

Best Boss Ever: I’ll have you know I’ve said many things to Kara, just last night we were discussing the merits of investing more heavily into the eco-friendly industry, in fact, I should check and see if she got my delivery of flowers as thanks, I appreciate the reminder.

Jess chuckled into her son’s head from where they were cuddled up for a family movie night in her own home. Lightning McQueen k-chowed and sped down the raceway as she shook her head at the paragraph her boss had just sent her on the numerous talks she had had with Kara just last week. 

“Useless,” she mused, deciding she had riled her boss up enough to last the weekend. Just until she saw her friend again on Monday.

Jess: 31

Lena: 0

\--

“Jess!”

The woman almost jumped, startled by Lena’s frantic yelling, and quickly ran into her boss’ office ready to face whatever danger lay ahead. 

Although she was not quite sure of how she could protect her boss from the dangerous wine catalogs she had spread around her in a circle on the floor.

“Uhhh…”

“Oh good,” Lena looked up with two catalogs in hand and carefully extracted herself from the organized chaos that was becoming her office floor, “I need your advice, do you think Kara would like the Roederer Cristal?”

Jess balked as Lena shoved the folded catalog marking the champagne in question, “Uh well I-”

“It is a bit of a dry champagne I know, not everyone is a fan but it has some nice floral and nutty peach notes and you do know how much Kara loved the flowers I sent her just last week,” Lena paced back to her stack, pulling even more catalogs from behind her couch.

“She uh well she did seem to enjoy the tulips-”

“But then the Chateau Petrus Pomerol is a much richer, more expensive drink, I’m sure her sister would appreciate that more than the champagne.”

Jess was nodding enthusiastically until of course her finger shifted revealing the price of the wine.

Holy shit.

WTF why in the world would a wine exist that costs half a million dollars...and that was before taxes! “That wine better sing, dance, and pay off my student loans every time I take a sip.” Jess quietly murmured

“What was that Jess?”

“Err, nothing but don’t you think you should pick something more Kara-ish, I’m sure all these spirits are lovely but we both know she loves nothing better than some potstickers and a tall glass of orange vanilla coca-cola,” Even though Jess would never understand how anyone could stomach the drink. 

Lena grew contemplative at the suggestion, catalogs practically spilling about around her feet as she made her way back to her desk.

Jess carefully picked her way through the mess, trying not to trip on the glossy paper so she could rest a reassuring hand on her friend’s shoulder. It dawned on her just how nervous Lena must be for her next hang out with the reporter. 

“Hey, it's just supposed to be a casual game night with friends right? I’m sure it will go great regardless of what you bring. Kara doesn’t care what you have with you, she just wants to have you-”

Lena looked up with anxiously wide eyes as Jess ran that sentence back through her head.

“There! She just wants to have you there, right?” 

Her boss took some much needed, calming, deep breaths finding her usual resolve, “You are right for once.”

Jess feigned a scoff catching on quickly to Lena’s own teasing smirk, “I’ll just be myself and everything will go fine, great even, though,” Lena trailed off looking up to Jess with her best pout. 

Jess rolled her eyes but conceded easily, “Yes Ms. Luthor?”

“...do you think you could help me pick out my outfit?”

\--

Lena repeated her pep talk in her head, it was fine, it would all be great. She was just officially meeting Kara’s closest friends and family as someone other than a work colleague.

No pressure.

Just as she was contemplating the merits of legging it back to her place and convincing Kara she had fallen ill, Alex Danvers, the not at all intimidating older sister opened the door with a wide maniacal grin on her face. Oh, joy.

Lena mustered up her best professional smile, if being a Luthor taught her anything it was how to maintain a fake outer exterior in uncomfortable situations. 

“Lena.”

“Alex.”

The two women stood, Practically staring the other down. Alex had yet to invite her inside and while she wasn’t a vampire Lena wasn’t about to barge in. She did still have her manners. 

She was saved by the bell when Winn walked up beside her, clapping her amicably on the back before doing the barging for the both of them, “I call Maggie for charades!”

Leaving Alex sputtering after the man, “Wha- she’s _my_ girlfriend!”

“Exactly and she’s the best at charades, you hog her every week it’s time for me to shoot my Schott as they say.”

The entire room groaned, leave it to Winn to break the ice. She smiled kindly at him and he sent a subtle nod. No doubt Kara had asked him to help run a bit of interference knowing how uncomfortable Lena would be leading up to this night and how Alex tended to be around the Luthor heiress. 

Right as she was beginning to overthink everything a familiar weight rested around her shoulders, she was enveloped in the scent of vanilla and pine, and she could feel her heart rate finally settle for the first time in hours. 

“Hey,” Kara squeezed her into her side in a one-armed hug, “I’m so glad you could make it.”

And suddenly all those excuses she almost used to get out of this evening seemed so stupid and trivial. How could she ever even contemplate escape when the alternative was being faced with the soft smile that Kara seemed to reserve just for her. 

She nearly responded saying she wouldn’t have missed it for the world but they both knew her nerves almost had her sprinting back out the door earlier. Besides, if there was one thing she’d never want to do, it was lying to Kara, “I- I’m glad I came too,”

From across the room they were both brought out of the moment from the sound of a snort and less than subtle, “That’s what she said.”

“ _Winn_ that is my sister!”

Kara bent over laughing as Winn ran from Alex’s murderous weapon of choice, dual-wielding two of Kara’s plush couch cushions. It was so comical and Kara’s joy was infectious, Lena couldn’t help but join in.

\--

“Oh, oh I know this All Dogs Go to heaven!”

“What?! No!”

“Sit down Schott time’s up!” James jumped up clutching the timer in success. Winn deflated while Maggie was stuck facepalming all the way back to her seat next to Alex.

“It was Cats! You know the critically acclaimed Broadway cult classic!”

“How was that Cats? It looked like you were trying to be a dog!”

“Oh I’ll show you a dog-” 

Kara stood up putting her body between the two friends even as Alex struggled to hold her girlfriend back and protect their tech friend from the detective’s wrath.

“Break! It's time for a break why don’t we get some more snacks and cooler heads, maybe take a cool ten minutes yeah?”

It was the first time Kara had really left her side all evening and Lena really had no reason to complain. So far she was having more fun than she could remember having during her entire childhood. 

Seeing the group disperse for a bit of air she decided she could use a top-up on her drink. Making her way to the kitchen it was not long until she found her back to the counter, literally cornered by Alex. A slightly tipsy Alex but still.

It was fine she and Jess had talked about how this could be a situation she ran into. She just needed to be sincere and maintain eye contact. Predators would strike at the first sign of weakness. 

She was psyching herself up, ready to rebut anything that came out of the older Danver’s mouth when the woman walked past her to bend down and reach behind the fridge, coming back up with a fresh bottle of wine. Lena was stuck with her jaw hanging from the speech she had prepared to recite but Alex simply held up a hand as she poured a fresh glass and placed the bottle into a cupboard.

Finally, the woman turned to face the Luthor and after a few seconds, she said one thing.

“Just, don’t fuck it up.”

That might be the most normal interaction she’d ever had with Alex and well, Lena was going to take it.

Alex left leaving Lena alone with her thoughts for all of half a minute when J’onn decided it was his turn to have some Luthor one on one time, “You know,”

While Lena was wary, knowing how involved the director of the DEO had been with her brother’s unfortunate past, his eyes held a warmness she’d always wanted from her own father and he was careful to give her the space she wanted, stopping to lean on the kitchen island giving Lena the entire open counter area.

With a sip from his cup he continued, “that may be the closest thing to approval I’ve ever seen from Alex.” From his smile, Lena would almost dare to say he seemed impressed.

“I know your brother and I don’t exactly have the best past, for many reasons but Kara has more than scolded me for not giving you a chance and tonight it was very easy to see,” He took a deep breath then maybe preparing himself, “you are more than your family name Lena, and I apologize that our interactions from the past were laden with my preconceived notions of your family. You’ve proven yourself with your actions and your words. You are a good person and I’m glad you’re now part of our little found family traditions.”

The young CEO was close to tears and it didn’t take much aside from J’onn offering his arms for them to share a short but sweet hug. No wonder Kara said he was basically a giant teddy bear. 

“I appreciate that more than you know, I’ve never really had a circle of close friends.”

She pulled away wiping away the bit of water that had gathered in her eyes with a handkerchief. 

Kara walked over from her corner where she totally was not eavesdropping in case Lena needed her for a quick escape. She was also a bit teary and soon Lena found a different set of arms encircling her, Kara’s voice just beside her ear, “You’re not getting rid of us anytime soon.”

“Awww group hug!”

Lena wasn’t entirely a fan of being a part of such a large group hug sandwich but she also found she couldn’t really complain either.

\--

The next day in the office found Jess smirking at her phone as Lena recounted a few moments from the night, like Alex’s weird little interaction and the heartfelt moment with J’onn, aww the oblivious baby gay was making strides. She was feeling like a proud parent seeing their baby bird fly for the first time. 

Her heart was warming with every interaction she read. Lena had texted her almost as soon as she got in for the night and then turned in to bed so Jess had yet to respond. She figured a quick early morning coffee run was in order, then they could talk all about it before the workday even began. Give Lena a chance to decompress as it were. 

It would not do to have her boss overthink every little thing from last night through the day and have a distracted mind during her meetings. Better to get her musings and analysis out now, and what better way than a girl talk. 

She hadn’t even told Lena she was planning on coming in early, the CEO was always early. She was sure Lena would appreciate the kind gesture. 

In fact, Jess was so busy being excited that she hardly noticed a few things, namely that Lena’s usual bodyguards seemed to be missing from her floor. Not even Meg making her usual patrol around as she tended to do in the mornings. 

No matter, she strolled confidently into Ms. Luthor’s office without even a knock. She’d come to regret that later.

There were many ways she saw her day going. As a personal assistant, she was organized, and part of that organization included having a plan and sticking to it as much as the day’s spontaneities allowed. 

Finding her boss topping Supergirl on the L-Corp office couch in a heated make-out session was nowhere near her top 10 list of what could happen today to upset Ms. Luthor’s schedule, yet here she was.

“M-Ms. Luthor?”

Jess practically yelped with shock, turning so quickly the coffees fell from the holder and onto the floor. With her super hearing naturally Supergirl was the first to notice and soon both of the mildly flustered and thoroughly disheveled women were panting with wide eyes at being caught.

“Jess, I- uh well I- wasn’t expecting you till 9 this morning.”

“Yeah, pardon my french but, no shit.” Kara snorted and tried to hide it behind her arm at Lena’s aghast expression but soon both women had dissolved into a fit of giggles at the situation while Jess was left staring decidedly at the very interesting tile pattern on the roof.

“Jess,” Lena made out as her giggles subsided, “please turn around.”

With a rather long exhale the assistant turned to the grinning women still trying to fight off the last of their mirth. 

“I didn’t intend for you to find out this way it's just, it’s all been so new with me and Kara and we just wanted to take some time for ourselves. Take it slow.”

Kara nodded quickly, in firm agreement, “I haven’t even told my sister yet and she is gonna _freak_.”

Lena looked down with a little flinch before finally meeting Jess’ eyes for the first time that morning, “Please don’t be mad?”

Really Jess could hardly blame them for that, they were young and in love with the added thrill of sneaking around. She can’t say she didn’t do her own fair share in high school...and college. It was how she met her wife after all. 

Jess gave her friend a quick squeeze and rub on the back, “No not mad just blindsided in the best of ways, Jeff owes me so much money.”

“What was that?”

“I was saying it is great to see you so happy and I already know Kara will treat you well. I’m not angry by any means but I want details! How did this even happen!?”

It took an hour or so, and Kara had to leave halfway through to make it to her own job on time but wow the two had been carrying on for almost a month under everyone’s noses.

So every time Jess thought she was pulling one over on her boss with a witty comeback or teasing remark about how much of a sheep she was...this whole time her boss was banging the pretty buff blonde hero of National City. Maybe even in her office...on the couch. She had sat on that couch just a few days ago! 

Screw the entire tally, clearly, Jess was the one who knew nothing when it came to oblivious women.

Lena: whatever the heck the final tally number is

Jess: 0

**Author's Note:**

> Happy Birthday, yesiamsleepy :finger_guns: from me, Nate and Fee
> 
> Btw, yes there is a wine that expensive and like holy shit...WHY


End file.
